Ethanol → 4'-(16-Hydroxyhexadecyloxy)biphenyl-4-carboxylic acid

HRID 231020Notes

Reaction equation

HRID 231020 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35]C(=O)C)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].C(O)C>O>[OH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 541844424'-(16-Acetyloxyhexadecyloxy)biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 198599774'-(16-Hydroxyhexadecyloxy)biphenyl-4-carboxylic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 m moles(15.7 g) of the above 4'-(16-acetyloxyhexadecyloxy)biphenyl-4-carboxylic acid ethyl ester and 10 g of sodium hydroxide were stirred for 10 min. at 70° C. in a mixed solution of 40 ml of ethanol and 80 ml of water. After the reaction, the reaction solution was concentrated to obtain 13.0 g of 4'-(16-hydroxyhexadecyloxy)biphenyl-4-carboxylic acid. (yield: 95%)

Workup

  1. customAfter the reaction
  2. concentrationthe reaction solution was concentrated

Sources & evidence

ORD record
ord-c2bcd08f64654292b3d26c7e768364f5
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

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