4'-Decyloxybiphenyl-4-carboxylic Acid → 4-Hydroxymethyl-4'-decyloxybiphenyl

HRID 1427

Reaction equation

HRID 1427 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(OCC)C>[OH:31][CH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:19][CH:20]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 114510854'-Decyloxybiphenyl-4-carboxylic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 190699634-Hydroxymethyl-4'-decyloxybiphenyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.81 g (21.34 mmol) of LiAlH4 was introduced into 40 ml of diethyl ether and stirred. To the mixture was dropwise added a solution, prepared by introducing 1.71 g (5.06 mmol) of 4'-decyloxy-4-biphenylcarboxylic acid obtained in the first stage of Example 11 into 30 ml of diethyl ether, at room temperature over a period of 2 to 3 minutes, which was then continuously stirred for 5 days. After confirming the consumption of the raw material by TLC, to the resultant mixture was added 40 ml of water, and further added concentrated hydrochloric acid until the aqueous phase was approximately homogenized. The resultant solution was extracted with diethyl ether and dried, to obtain 4-hydroxymethyl-4'-decyloxybiphenyl.

Workup

  1. additionTo the mixture was dropwise added a solution
  2. customprepared
  3. stirringwhich was then continuously stirred for 5 days
  4. customthe consumption of the raw material by TLC
  5. additionto the resultant mixture was added 40 ml of water
  6. additionfurther added concentrated hydrochloric acid until the aqueous phase
  7. stirringwas approximately homogenized
  8. extractionThe resultant solution was extracted with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-c8e403a545964087ba37eaf4049bc15b
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Linked notes

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