1-Octanol → Octyl hydrogen phthalate

HRID 903486Notes

Reaction equation

HRID 903486 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].C(O)CCCCCCC.[C:21]1(=[O:31])[O:26][C:24](=[O:25])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[SiH4]>C(O)CCCCCCCCC.C(O)CCCCCCC.C(N(CC)CC)C>[C:21]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])(=[O:31])[C:22]1[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:24]([OH:26])=[O:25].[C:21]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:31])[C:22]1[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:24]([OH:26])=[O:25]

Participants

8

Reactant 4

HCID 9571-OctanolHCID 6811Phthalic AnhydrideHCID 81741-Decanol2×HCID 23953Silane

Product 2

HCID 79362Octyl hydrogen phthalateHCID 905341,2-Benzenedicarboxylic acid, 1-decyl ester

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 18772455HCID 18772455, compoundSolvent

Procedure

Solution I, a 50 percent solution of octyl hydrogen phthalate and decyl hydrogen phthalate in mixed 1-decanol/1-octanol was prepared by heating a mixture of 82.4 g. of Epal 810 (a commercially available mixture from Ethyl Corporation of approximately half 1-decanol and half 1-octanol), 29.6 g. of phthalic anhydride and 1 g. of triethylamine up to 120° C. Then 1.46 parts by weight of solution I was combined with 1 part by weight of the 50 percent hydrolyzed silane (1) solution described in Example 7 to give solution II containing 1 mole of carboxylic acid per mole of primary amino group.

Workup

  1. temperatureby heating
  2. additiona mixture of 82.4 g
  3. customup to 120° C
  4. customto give solution II

Sources & evidence

ORD record
ord-3a4dc7a36b624eff8c62973dc94854e7
Source dataset
uspto-grants-1980_10
Patent number
US04228061

Reaction notes

Loading…