Sulfuric Acid → HCID 53997885, compound

HRID 744786Notes

Reaction equation

HRID 744786 reaction equation
C([O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][C:11]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.OS(O)(=O)=O>O1CCCC1.O1CCCC1.O>[CH2:21]([O:20][C:11]1[CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][OH:8])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 53645944HCID 53645944, compound

Product 1

HCID 53997885HCID 53997885, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 6.44 g of 2-benzyloxy-4-tert-butylbenzoic acid benzyl ester in 10 ml of tetrahydrofuran is slowly added dropwise to a suspension, stirred at room temperature, of 0.47 g of LiAlH4 in 40 ml of tetrahydrofuran. The reaction mixture is stirred for a further 4 hours at room temperature and then, in succession, 0.96 ml of ethyl acetate, 6.4 ml of tetrahydrofuran/water=1:1 and 9.6 ml of 2N H2SO4 are added dropwise thereto. The suspension is partitioned between ethyl acetate and water/saturated sodium chloride solution, the organic phases are concentrated by evaporation and the residue is purified by means of FC (150 g of silica gel, dichloromethane/hexane=6:4). Title compound: Rf (dichloromethane/hexane=8:2)=0.24.

Workup

  1. customThe suspension is partitioned between ethyl acetate and water/saturated sodium chloride solution
  2. concentrationthe organic phases are concentrated by evaporation
  3. customthe residue is purified by means of FC (150 g of silica gel, dichloromethane/hexane=6:4)

Sources & evidence

ORD record
ord-cc315422971e41f29d91f3861a23a4b2
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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